Ethanolamine → 2-((Triphenylmethyl)amino)ethanol

HRID 1449431Notes

Reaction equation

HRID 1449431 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].C(N(CC)CC)C.Cl[Si](C)(C)C.Cl[C:18]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O1CCCC1>[C:19]1([C:18]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[NH:4][CH2:3][CH2:1][OH:2])[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 700EthanolamineHCID 6397ChlorotrimethylsilaneHCID 6456Trityl chlorideHCID 8471Triethylamine2×

Product 1

HCID 31256082-((Triphenylmethyl)amino)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Ethanolamine (5 g, 82 mmol) and triethylamine (11.4 ml, 8.28 g, 82 mmol) were dissolved in dry tetrahydrofuran (50 ml). Chlorotrimethylsilane (10.4 ml, 8.90 g, 82 mmol) was added over five minutes and the mixture was stirred for 30 minutes. The white solid was removed by filtration and washed with dry tetrahydrofuran. The combined filtrate and washings were stirred and triethylamine (11.4 ml, 8.28 g, 82 mmol) was added followed by chlorotriphenylmethane (22.8 g, 82 mmol). The mixture was stirred at ambient temperature for two hours, when it was filtered and the filtrate cooled to 0° C. for 30 minutes. Following a further filtration the liquors were stirred with methanol (60 ml) for fifteen minutes. The solvent was removed under vacuum and the residue crystallised from hot ethyl acetate. The resulting white solid was dried under vacuum at room temperature for 16 hours before triturating successively with diethyl ether (twice) and acetone (twice). The residue was heated with boiling acetone (700 ml) for ten minutes before the solid was collected by filtration, washed with cold acetone and dried under vacuum for four hours to give N-(triphenylmethyl)ethanolamine.

Workup

  1. customThe white solid was removed by filtration
  2. washwashed with dry tetrahydrofuran
  3. stirringThe combined filtrate and washings were stirred
  4. stirringThe mixture was stirred at ambient temperature for two hours
  5. filtrationwhen it was filtered
  6. filtrationa further filtration the liquors
  7. stirringwere stirred with methanol (60 ml) for fifteen minutes
  8. customThe solvent was removed under vacuum
  9. customthe residue crystallised from hot ethyl acetate
  10. customThe resulting white solid was dried under vacuum at room temperature for 16 hours
  11. custombefore triturating successively with diethyl ether (twice) and acetone (twice)
  12. temperatureThe residue was heated with boiling acetone (700 ml) for ten minutes before the solid
  13. filtrationwas collected by filtration
  14. washwashed with cold acetone
  15. customdried under vacuum for four hours

Sources & evidence

ORD record
ord-8e9f1ce60bed4adeabde1b2471639248
Source dataset
uspto-grants-1997_02
Patent number
US05599587

Reaction notes

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